PMID- 37642717 OWN - NLM STAT- MEDLINE DCOM- 20231012 LR - 20231018 IS - 1432-0614 (Electronic) IS - 0175-7598 (Linking) VI - 107 IP - 21 DP - 2023 Nov TI - Novel citrinin derivatives from fungus Penicillium sp. TW131-64 and their antimicrobial activities. PG - 6607-6619 LID - 10.1007/s00253-023-12738-3 [doi] AB - Six new citrinin derivatives (1, 2, 4, 10, 11, and 16), along with fourteen known analogues, were acquired from Penicillium sp. TW131-64, a marine-derived fungus strain. The chemical structures of new compounds were identified through adopting various spectroscopic methods in combination with X-ray diffraction technology and comparison of the experimental electronic circular dichroism (ECD) with calculated ones. Among them, compounds 1-4 were nitrogen-containing citrinin derivatives existing in enantiomers which were resolved by chiral chromatography. A putative biosynthetic pathway for compounds 1-4 was proposed. Additionally, the antimicrobial activities of these compounds were detected by the broth microdilution assays. Citrinin derivatives 1, 2, 4 and their corresponding enantiomers (1a, 2a, 4a, 1b, 2b, and 4b) exhibited potent antimicrobial activities towards Helicobacter pylori standard strains and multidrug-resistant strains (MIC values ranging from 0.25 to 8 mug/mL), which were comparable or even better than metronidazole. Moreover, compounds 1a and 1b also showed remarkable broad antimicrobial effects towards Staphylococcus aureus, Enterococcus faecalis, methicillin-resistant Staphylococcus aureus (MRSA), Bacillus subtilis, vancomycin-resistant Enterococcus faecium (VRE), and Candida albicans. In summary, our studies demonstrated that citrinin enantiomers 1a-4a and 1b-4b, especially 1a and 1b, can be lead compounds in the research and development (R & D) of novel antimicrobial drugs. KEY POINTS: * 3 novel nitrogen-containing citrinin derivatives (1, 2, 4) were isolated. * citrinin derivatives 1-4 in enantiomers were resolved by chiral chromatography. * citrinin derivatives 1a and 1b showed broad and significant antimicrobial effects. CI - (c) 2023. The Author(s), under exclusive licence to Springer-Verlag GmbH Germany, part of Springer Nature. FAU - Lai, Changrong AU - Lai C AD - Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy/Guangdong Province Key Laboratory of Pharmacodynamic Constituents of Traditional Chinese Medicine and New Drug Research/International Cooperative Laboratory of Traditional Chinese Medicine Modernization and Innovative Drug Development of Ministry of Education (MOE) of China, Jinan University, Guangzhou, 510632, China. FAU - Tian, Danmei AU - Tian D AD - Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy/Guangdong Province Key Laboratory of Pharmacodynamic Constituents of Traditional Chinese Medicine and New Drug Research/International Cooperative Laboratory of Traditional Chinese Medicine Modernization and Innovative Drug Development of Ministry of Education (MOE) of China, Jinan University, Guangzhou, 510632, China. FAU - Zheng, Mingxin AU - Zheng M AD - Department of Pathogen Biology, Jiangsu Key Laboratory of Pathogen Biology, Helicobacter Pylori Research Centre, Nanjing Medical University, Nanjing, 211166, China. FAU - Li, Binglei AU - Li B AD - Department of Pathogen Biology, Jiangsu Key Laboratory of Pathogen Biology, Helicobacter Pylori Research Centre, Nanjing Medical University, Nanjing, 211166, China. FAU - Jia, Jia AU - Jia J AD - Department of Pathogen Biology, Jiangsu Key Laboratory of Pathogen Biology, Helicobacter Pylori Research Centre, Nanjing Medical University, Nanjing, 211166, China. FAU - Wei, Jihua AU - Wei J AD - Ocean College, Zhejiang University, Zhoushan Campus, Zhoushan, 316021, China. FAU - Wu, Bin AU - Wu B AD - Ocean College, Zhejiang University, Zhoushan Campus, Zhoushan, 316021, China. wubin@zju.edu.cn. FAU - Bi, Hongkai AU - Bi H AD - Department of Pathogen Biology, Jiangsu Key Laboratory of Pathogen Biology, Helicobacter Pylori Research Centre, Nanjing Medical University, Nanjing, 211166, China. hkbi@njmu.edu.cn. FAU - Tang, Jinshan AU - Tang J AUID- ORCID: 0000-0003-0150-0595 AD - Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy/Guangdong Province Key Laboratory of Pharmacodynamic Constituents of Traditional Chinese Medicine and New Drug Research/International Cooperative Laboratory of Traditional Chinese Medicine Modernization and Innovative Drug Development of Ministry of Education (MOE) of China, Jinan University, Guangzhou, 510632, China. gztangjinshan@126.com. LA - eng GR - 2022YFC2804101/National Key Research and Development Program of China/ GR - 2023A1515010432/Guangdong Basic and Applied Basic Research Foundation/ GR - 202201010305/Guangzhou Basic and Applied Basic Research Foundation/ GR - 82073899/National Natural Science Foundation of China/ PT - Journal Article DEP - 20230829 PL - Germany TA - Appl Microbiol Biotechnol JT - Applied microbiology and biotechnology JID - 8406612 RN - 3S697X6SNZ (Citrinin) RN - 0 (Anti-Bacterial Agents) RN - 0 (Anti-Infective Agents) RN - N762921K75 (Nitrogen) SB - IM MH - *Citrinin/pharmacology MH - Anti-Bacterial Agents/chemistry MH - *Penicillium MH - *Methicillin-Resistant Staphylococcus aureus MH - Fungi MH - *Anti-Infective Agents/pharmacology MH - Nitrogen/pharmacology MH - Microbial Sensitivity Tests MH - Molecular Structure OTO - NOTNLM OT - Citrinin derivatives OT - Marine-derived fungus OT - Penicillium sp. TW131-64 OT - Secondary metabolites OT - antimicrobial activity EDAT- 2023/08/29 12:43 MHDA- 2023/10/12 06:43 CRDT- 2023/08/29 11:08 PHST- 2023/04/06 00:00 [received] PHST- 2023/08/21 00:00 [accepted] PHST- 2023/07/05 00:00 [revised] PHST- 2023/10/12 06:43 [medline] PHST- 2023/08/29 12:43 [pubmed] PHST- 2023/08/29 11:08 [entrez] AID - 10.1007/s00253-023-12738-3 [pii] AID - 10.1007/s00253-023-12738-3 [doi] PST - ppublish SO - Appl Microbiol Biotechnol. 2023 Nov;107(21):6607-6619. doi: 10.1007/s00253-023-12738-3. Epub 2023 Aug 29.